ammonia; hydrogen; NiB, 10 percent in ethanol T=60 - 70°C; Reduction; amination; P=76000 Torr;

ammonium cerium(IV) nitrate in water; acetonitrile T=0°C; 0.25 h;

1: 1.) n-BuLi, 2.) BF3-Et2O / 1.) THF, HMPA, -72 deg C, 30 min, 2.) -72 deg C -> 0 deg C, 2 h 2: 1.) t-BuOK, 2.) TsCl / 1.) HMPA, THF, 0 deg C, 1 h, 2.) 50 deg C, 3 h 3: 55 percent / CAN / acetonitrile; H2O / 0.25 h / 0 °C View Scheme

1: 1.) t-BuOK, 2.) TsCl / 1.) HMPA, THF, 0 deg C, 1 h, 2.) 50 deg C, 3 h 2: 55 percent / CAN / acetonitrile; H2O / 0.25 h / 0 °C View Scheme